


You had a boyfriend

by steadybeholder



Series: Somebody told me [1]
Category: Supernatural
Genre: AU, Alternate Universe - High School, F/F, F/M, M/M, Playing Cupid I guess, Romance, Shipping
Language: English
Status: In-Progress
Published: 2014-09-08
Updated: 2014-09-08
Packaged: 2018-02-14 23:49:47
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,329
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2207652
Author URL: https://archiveofourown.org/users/steadybeholder/pseuds/steadybeholder
Summary: <blockquote class="userstuff">
              <p>It's not exactly a crush but Jess has known Sam for years and has a thing for him. She's 97% sure he's gay but Sam's brother tells her not to try anything and Sam's ex looks at her as if he wanted to murder her laser-eye style.<br/>Sooo... Sam's gay, right?</p><p>Here's the first part of a fic in which:<br/>Dean (and his bff, Charlie) try to get Sam and Jess together.<br/>Sam and Jess try to get Dean and Cas together<br/>And Gabriel tries to get- well, tries to get back with Sam.</p>
            </blockquote>





	You had a boyfriend

**Author's Note:**

> And so it begins.  
> Jess' POV

**Summary for the Chapter:**

> Jess makes her move.  
> Just because the guy she has a thing (crush) on is gay doesn't mean she can't be friends with him.  
> (Because he is gay, right?)

Sam and I had been in the same classes I believe since the eighth grade when I moved from California, and I can say as a matter of fact, that I knew he'd be really good looking back then when people made fun of his braces and shaggy hair. At some point during summer break around those years, he must have been visited by the puberty fairy (it visits everyone so don't worry, you're probably still on queue) because he came back and boy was I right. He was built up and his braces were gone. His smile had always been cute but now it shone more than ever. The messy hair was still there but now it played in his favor (it was also a bit shorter now). Yup, all the girls (and boys) had to swallow their words and suddenly everyone wanted to be around this adorable moose, and you know the best part? He never stopped being nice. Before _and_ after _Extreme Makeover: Sam Edition._ Of course, he being so adorable now that his face matched his personality so well made him incredibly noticeable to the ladies (myself kind of included). Aaand that was when we all got the not-so-adorable news: He was taken. By another guy. Don't get me wrong, I was totally fine with boys dating boys. It was the idea of Sam Winchester _not_ dating girls that was kind of a letdown. Not that I was keeping my hopes up or anything. Probably the only thing we had in common were our shared classes.

Gabriel was fine, I guess. I swear I wasn't jealous. He just seemed a bit- wrong? No, that’s not the word. Sam was totally swept off his feet by this guy who was a couple years older and super cheeky with a bad boy attitude and, since everybody loved Sam, everyone was happy just seeing him smile the way he did when they were together. They looked cute. But they didn't make complete sense before my eyes. Yes, yes, it sounds like I want you to believe I have some sort of enhanced perception or something. But hey, they did not break up over _nothing_. So I guess I was right about that too. It was weird how I had known Sam for years and we had barely spoken in all that time. You could say I was in the _“Sam’s awesome and we love him but we don't talk so we're kind of like his fans”_  club. Ok, I didn't _love_ him, and I wasn't really his _fan._ I just happened to like him a lot without having really talked to him. Trust me, if you knew him, you'd feel the same way.

So, here we are. Six good months after the news of Sam and Gabriel breaking up spread throughout the entire school. As far as I know, he never talked about it, but the fact of having strangers chatting about his love life didn't seem to bother him either. Physics class was coming to an end and luckily it was almost lunch time (I forgot to have breakfast that morning so my stomach’s noises were turning up a little bit too loud). Sam was sitting somewhere in the last row. He’s so big he didn't want his tall figure blocking anyone’s view of the board, see what I mean?

“We're almost done, Gary. Just hang in there”, the class erupted into laughter after the teacher made what I believe was his fifth attempt of keeping Garrett Coleman awake. Either the poor kid never got enough sleep at home, or he got _really_ bored with Mr. MacLeod’s class, I don't know but it still amazes me how he hasn’t smacked the boy’s head with a book yet, it doesn't seem like he's lacking of intentions to do it.

“I know you hot blooded people need a way to keep your minds busy, otherwise you recur to unhealthy methods of entertainment. So I'll proceed to make my contribution to society”, yeah, I know where this is going, “From the exercises in page 83, do the odd numbers”

A series of _‘Aw’_ s and ‘ _seriously?_ ’s flew across the classroom as some people opened their books (for the first time in the entire hour), not exactly on page 83.

“Don't bother, smarty pants. You won’t find the answers at the end”, Mr. MacLeod smiled mischievously, I bet he thinks he’s the evilest man on Earth. “Enjoy your weekend. Class dismissed”

The guy’s a lame bastard, but not liking him is nearly impossible.

That was when I took a last look at the board, blocked from time to time by the students that made their way out of the classroom, heading to the cafeteria, and silently gasped with the realization that I had _absolutely no idea_ of what was written there. I know it couldn't have been that hard to understand. If only I had actually _been_ to the last three classes. But nooo, I wasn't here. I was home. Sick. And barely surviving with chicken soup and Meg Ryan movies, believe me when I say, Mononucleosis is _the worst_ (note to self: do NOT play spin the bottle EVER-AGAIN. I can't get it twice but I won't take risks with other infectious crap). My dad told me it was of no use to skip classes almost the entire week and show up on a Friday like nothing happened, that I should've waited ‘till Monday. But hell was I lost after only three days, I don't think coming to school on Monday with no homework and no clue of what it was about would've been any better.

 _Ok Jess, think. Who can get you out of this?_ One time I asked for a tutor during finals and the asshole tried to get from me way more than my number. Some people just don't take rejection that well. He told all of his friends (and his friends told their friends) that it was impossible to tutor me since I was, quote: _“A dumb blond that won't let you touch her unless you improve her grades”_ I was so pissed off I wanted to go beat the living crap out of him, not that I was actually capable of doing so but I could've learned kick boxing or some martial art just to teach him a lesson (or save the time and find someone who could do just the same for me). A year and a half later I still couldn't shake that reputation off completely. What I'm trying to say here is, no tutors for me, thank you very much. Sooo, back to the _who-can-get-me-out-of-my-confusion-pit_ subject. I mentally went through all the people in that class that I knew; there weren't that many to be honest. None of my actual friends were there (and by actual friends I mean ‘people I spend most of my time with’). I knew Gary but, as you could already tell, he was not a reliable source of Physics explanation; there were two or three people I had talked to before, more like they had talked to me, to ask me for my notes from previous classes, somehow I didn't trust them to help me out either. That left me with only one (and obvious) option: Sam. He hadn't left the room yet; he was with Gary, letting him take pictures of his notes with his phone since Mr. MacLeod had just erased what was written there before leaving as well.

“Thanks, man. See you later”

“Don't worry about it”

Gary threw his backpack over his shoulder and got out of the classroom, only after raising his eyebrow at me and giving me that flirty smile of his that is more like a grimace than an actual gesture, he only kept doing it because it made me laugh, just like this time. Sam turned to look at me, he probably wondered why I was still there, after Gary left we were the only two people in the room.

“Hey, Jess. How are you?” He said with a smile, closing his notebook without looking at it. I think I smiled back.

“Um, fine, I guess” Woah, Jessica. You're great with words, seriously.

He chuckled. What.

“I mean, your health. I heard you were sick. You fully recovered now?” I dare you to tell me he’s not sweet. Go on, try it.

“Oh, yeah. Mono. Worst days of my life, I swear” That got a tiny laugh from him. I wondered why weren’t we friends, it felt good to talk to him. Then I saw him getting kinda tense, maybe I was making him uncomfortable. I always wondered how he dealt with the girls that kept flirting with him, not knowing that he didn't play for that team. But hey, I wasn't flirting. I almost forget why I wanted to talk to him in the first place, though.

“Um, Sam?”

“Yeah?”

“You think you could help me out with um- eh…”

“The assignment?” he raised his eyebrows.

“The whole lesson, actually” It wasn't my thing to ask for help, really. The first and only time I had gathered enough courage to swallow my pride and ask for a tutor I had crashed, face first into a douchebag with zero morals. So it was a pretty big deal for Jessica Moore to ask someone to explain an entire class to her. Sam just replied with a half-smile, crossing the strap of his bag over his chest from his left shoulder to his right side.

“Sure”

“Really? Thank you so much”

“It’s pretty easy, you’ll get it all real fast” I wouldn't mind not seeing Mr. MacLeod ever again, give me Professor Winchester any day.

_Stop it, Jess. He’s gay, remember?_

_Sigh_

* * *

 

I might or might not have gotten some ketchup on Sam’s notes during lunch.

He didn't mind.

“Wait, so that’s it?” I asked incredulous “cos for x and sin for y?” I could feel the blood rushing to my face, heat in my cheeks. God, I felt stupid.

“And multiply for the distance between the force and the point. I told you it was easy”, he replied, probably marveling at how I seemed to have discovered warm water.

“If that’s it then, I won't bother you anymore. You probably want to go finish lunch with your friends” I was already getting up but-

“Actually”, he spoke fast before I leave, “I was wondering, if you have nothing to do after school, maybe we could, get together and do the exercises, you know, to get this out of the way”

He seemed nervous. Was he just naturally shy or was there another reason? I don't think I make people nervous. I had always believed Sam was this easy talking guy that was always so sure of himself. Seeing him act so lost was something new, but also kind of amusing.

Wait, did he just ask me to do homework with him? If I didn't know he wasn't into girls, I'd be 97% sure that it was a lame excuse to hang out with me. And since I know it's not that... is he just  _that_ responsible?

“I knew you were the good student type but, have I encountered the lost species of ‘ _do-homework-on-Friday-Sapiens’_?”

He looked down and laughed, if possible more nervously at that. Damn, he was cute. Cute _and_ gay. Life isn't fair now, is it?

“Don't tell anyone. They might want to lock me down and experiment with my brain” That got a smile from me this time, followed by more frustration.

_Stop being so perfect, damn it._

But why did it bother me so much? I didn't like him that way. Not that I was aware of. _But-_ I thought, _that can't stop me from being his friend, right?_ _I bet he’s the kind of friend that will listen to all of your problems and spend sleepless nights looking for a way to solve them, calling you at random hours just to see how you are_. As a person with not so many close people to her, I was seriously starting to fantasize about being Sam’s friend. Yeah, I know, pathetic.

“Don't worry”, I said in a quiet voice, “your secret’s safe with me”

“So”

“So?”

“Homework. After class?”

“Oh! Right. Sure. Your place?”

“Why not yours?”

_Because my mom will repeatedly point out how good looking you are and then ask why don't you date me, and my dad has heard enough about you to embarrass me for the rest of my life._

“I find it really hard to concentrate at my house”

“Ok then. My place it is”

We spent the rest of lunch time talking. He told me about his brother and his uncle- well, it wasn't really his uncle but a close friend of his father’s. It surprised me how light heartedly he spoke about his dad leaving him and his brother after their mother died. He said he doesn't even remember him very well, but he sure would love to remember his mother’s face. He also apologized beforehand for whatever inappropriate commentary his brother might do during dinner.

“Are you already asking me to stay for dinner?” I asked, smirking.

“Will you?”

I smiled and nodded in response.

He seemed pretty happy and proud of his family. Bobby was the name of his uncle, he had taken care of him and his brother for as long as he could remember. Bobby married a woman named Ellen when Sam and Dean were little, she had a daughter from a previous marriage, Jo; her husband had passed away not long after the girl was born. So it was Bobby, Ellen, Jo, Dean and Sam. It was a lovely picture in my head.

There wasn't much to talk about on my side. It was my sister, my parents and me. No perfect family picture, more like a dramatic mix between Malcolm in the Middle and Little House on the Prairie but we were fine. My sister got into a fight with my mom, moved to Italy when she turned eighteen three years ago and we haven't heard of her since then so there’s that too.

“Aren't you afraid that something might’ve happened to her?” he asked, genuinely concerned

“Not really” he opened his eyes wide at my response, I laughed a little “When I said _we_ haven't heard anything from her I meant _my parents_. It’s just that they're not supposed to know I talk to her. I was just repeating the story”

“So she’s ok, then?” he let out a sigh of relief

“Yeah, she’s got a girlfriend, an apartment, a job, even a cat named Sweater” I said with a smile on my face. I've skyped with Jane and her girlfriend, Angie; they seem so happy. I wish mom and dad could see that too. Jane and dad never argued, it was just that she didn't trust him not to tell mom that they stayed in touch so she preferred not to make him keep secrets from mom.

On a side note, my sister going MIA from my parents wasn't really the biggest drama going on for the Moore's. Sometimes I envied and resented Jane for leaving me here with my mom's mental issues. At times she would forget to take her pills and whoever stood in her way would pay the price. My dad didn't want to be with her anymore, he has told me that he wanted to file for the divorce even before Jane left but it was too late now; he wouldn't leave her because she needs someone to take care of her and we can't afford to pay a nurse to do so. That's actually the main reason why I don't spend at home any more time than the strictly necessary.

However, I didn't tell Sam about that. I didn't want him thinking that I wanted pity or attention. There are things in your life that other people simply don't have to know.

* * *

The next few classes seemed to have no end. It was Friday after all. Poor Mr. Shurley, being the last teacher a student sees on Friday grants you total and complete hatred once the clock begins teasing the students with the last few minutes.

“I bet Fergus gave you enough work to have a blast  for the weekend so I'll take care of your miserableness on Monday”, Chuck closed the brown hard cover book he was holding and walked to the bag that was sitting on his desk. He had been holding that book during the entire class but not even once he mentioned what it was about or read something from it. Dramatic purposes I guess.

"Go on. I'm setting you free"

Everybody got up and left the room at the speed of light. Creative Writing was an elective so it was supposed that everyone in the class was there by choice. The teacher didn't mind, he seemed like the kind of person who didn't lose sleep over people’s opinions, he loved what he taught and he was good at teaching. Some students left with _‘Bye, Chuck’_ s and _‘See you on Monday’s._ Others just walked past him as if he were invisible, not much different from what they do while he’s talking.

“’Till Monday, Chuck” I took my bag and walked to the door.

“Oh, goodbye Jess” I heard him say before I left.

When I crossed the doorframe, Sam was right outside.

“Have you been waiting for me to get out? Did you know I was in this classroom?” I raised an eyebrow and held the straps of my backpack with each hand. He laughed.

“I have classes just next door” he replied “You ready?”

I nodded and we walked to the school’s parking lot. An old Nissan was parked right beside the bike rack.

“That one” he pointed at it without hesitating, sounding almost proud of the brown, dusty car with paint peeled out at the edges.

“Fancy” I said, smiling at his cute pride. I walked to the passenger seat door but Sam rushed to open it for me. “I can do it”, I said, stretching my arm to the handle.

“But I want to”, he insisted. And I let him. I got in the car, he did the same and we took off to Sam’s house.

Sam’s uncle and brother work together at a garage and the three of them spent an entire summer fixing that car together. They gave him the car as a birthday present after he got his license. Why he hadn't painted it yet remained as a mystery to me.

* * *

 

Sam’s house seemed to be like out of a fifties family TV show. A white and green, old but well taken care of house in the suburbs made almost entirely of wood.

“Cool, Dean’s not here yet. I get the parking space” I heard him say as he entered the front yard and placed his car at the one vehicle spot at the left of it.

I remember Dean Winchester’s Car. _Gorgeous._ I believe it was a Chevy, not sure what model but it was a classic and a total sensation with girls, not like Dean Winchester needed any help getting girls. He used to pick Sam up in his car and just now I remember the Chevy stopped showing up at the parking lot around 11th grade; I guess that’s when Sam got his own car.

“Stay there” he said to me once he stopped the engine and got off the car.

“Um, ok?” I replied.

He walked/ran to the passenger seat door and opened it for me. I just laughed and got out.

We walked to the porch, up the three steps that led to the front door and, yes, you guessed right, he opened it for me. “Thank you very much”, I said, laughing as I walked through the doorframe.

“Ellen, I'm home” he spoke up and we heard footsteps coming our way.

“Did Jo tell you-? Oh, who is this pretty girl, Sam?” A middle aged woman, I assume that was Ellen, walked towards us and stopped on her heels, grinning when she saw me. She was wearing Jeans, black boots and a plaid long sleeved shirt over a black top. If I didn't know who Ellen was and weren’t sure that it was Sam’s house, I would've believed the woman in front of me didn't really live there.

“Ellen, this is Jess. Jess, this is Ellen”

I walked forward and stretched my hand, smiling. “Sam has told me about you. It's a pleasure to meet you”

She did the same and shook my hand, smiling back. “I believe I've heard about you too”

 “Have you?” I turned to Sam and raised an eyebrow.

“Er- yeah- I mean- I might have mentioned you once or twice” Sam began “We're in the same classes after all. And well- you got mono this week so I think I brought that up during dinner sometime”. He sure blushes a lot talking to me, you know, for being a guy who’s not into girls.

“Anyway” Ellen tried to break the awkward silence “Sam, did Jo tell you where she was going? She’s not returning my calls”

“Oh, yes. She told me her phone was almost dead. She went to Becky’s with Meg to study for a test tomorrow”

“I'll call Becky’s house later then”.

Sam chuckled at the worried mother, “Ok. Oh, and speaking of, we’ll be doing homework here. Jess is staying for dinner”

“Just in time. I was about to start cooking”

“Isn't it Uncle Bobby’s turn?”

“I lost a bet with him over a football game. It’s my turn today. And tomorrow” she said with a sigh.

I smiled. I wanted to laugh, but I didn't feel like I should. “You and your husband seem to have a fun relationship”

“It better be”, she answered “Ten years are no walk in the park. Sam, will you stay in the living room?”

“No, we’ll work in my room”

Ellen frowned and raised an eyebrow at him, putting her hands on her hips. “Doors opened, right?”

“Eh- Ellen!”

“You know the rules, Sam. _Not in my house_ ”

“That’s not-! We’re not-! Ugh, fine”

That took me by surprise. Although Sam’s frustration was kind of entertaining. Either way, why does it matter if the doors are closed or not? It’s not like we'll be doing something inappropriate. Sam and Gabriel were together for a year and everyone in school knew that; I don't believe Ellen didn't know about Sam's preferences.

“Ok, what was that?” I asked while we went upstairs, Sam was in front of me (I might or might not have glanced at his behind once or twice until we arrived to the second floor. What?)

“Um, just- house rules”

“But doesn't she know-?”

“Know what?”

“Nothing”

After we reached the end of the staircase we entered the first door to the right.

 Sam turned the lights on. I took a seat at the empty chair in front of his desk and placed my bag on the floor; he sat at the edge of his bed, with his left leg folded over it and his right foot on the floor.

Sam’s room was a lot cleaner and better organized than mine, good thing we were here and not in my house. The walls were white except for the one where the door was, which was painted with a light green. No posters or family pictures on the walls, only a huge world map hung above his bed; some places were pinpointed, inside the country or across the oceans, the ones inside the U.S. had green pins and the ones outside of it were blue. However he did have pictures sitting on his desk and on his shelves, mixed with books and some trophies whose tags I couldn't read; I recognized Dean and Ellen in them, I assumed the man with a beard and a cap was his uncle Bobby and the blond girl with Sam and Dean was Jo. I kind of expected to see a picture of his dad but it was nowhere to be seen, same with his mom; then I remembered he told me he had no memories of his mother’s face, which meant he had never seen pictures of her.

“Shall we begin?” Sam spoke, bringing me back from my thoughts.

“Yeah, ok. I- No way, I love this book!” I took the copy of The Little Prince that was standing in a corner of his desk, causing other books to fall from their place, but I was too excited eyeing an edition of my favorite book I had never seen before to be the least embarrassed by the mess I had just made.

“Really? Me too!” he responded, not paying attention to the books that were now scattered on the corner of his desk either.

“What’s the story?”

“What?”

“ _Your_ story with the book”, I replied. Every person I know who has read The Little Prince has a story about it. Like, how they got it or what it did to them. I have never met someone who has told me _‘Oh, I read it. It was fine’_ and that’s it. No, there’s always a story.

Sam’s eyes lit up at a sudden memory, a smile appearing on his face little by little until his teeth were on sight.

“Dean got it for me”, was his response, “I was ten at the time and we had argued over something really stupid, I don't even remember what it was. I ignored him for two days straight until he got home with this book and said _‘Here. You’ll like it’_ ” he let out a short laugh, “it sounds like he bought my forgiveness. Anyway, I read the book in three nights and with each page my anger would disappear bit by bit. I remember wishing to be like the Little Prince, and travel through space visiting planets and stars. But then I realized I had much more than him and still didn't cherish it as much as he did. I felt jealous at his ability to celebrate little things and made a promise to myself that I would do just that from that moment on. When I finished reading I asked Dean why he had given me that book, being that the first time I spoke to him in a week. He just shrugged and said he had read it at school when he was little and imagined me as the Little Prince. That day on the way home he had seen it at the window of a bookshop. He wasn't trying to make me forgive him for the stupid argument, he just had wanted me to read the book from the moment he read it”

Silence followed Sam’s story, it was so sweet. I envied Sam for having his brother with him. I missed Jane so much.

“I had never thought about that as a story”, he said, “never really made the connection”

“I told you” I smirked, taking proud on the fact that I had made him realize something important “there’s always a story”

“What’s yours, then?”

 “I guess you beat me” I said “I was twelve when I read it. My Language teacher had just sent me to the principal’s office because I told her the class was boring and I wasn't learning” Sam laughed “I was so annoyed by the teacher that I convinced myself that everything she told us was wrong, even when she sent us to read books, I hated books because I thought that reading them meant obeying her and that was something I did not want to do”

“So you decided to overthrow the government” Sam said, still grinning.

“Shhh! Let me finish. When I got home and told my dad what happened he asked me if there were any books I'd like to read and when I said no he handed me his own copy of The Little Prince. Once I realized that books and teachers didn't exactly go hand in hand, I started getting better at Language and reading more books, looking for more stories like that and even wanting to make stories of my own. Actually, The Little Prince is the reason why I want to be a writer”

“Whoa, I had no idea, Jess”

I smiled and nodded.

“I guess your story is better than mine, actually”

“I wouldn't say so. You creating bonds with your brother is actually a better story than my spoiled brat stage”

“Yeah, twelve year old you sounds very annoying, actually”

I gasped in response, arching my eyebrows and bringing my right hand to my chest, seeming offended.

“In my defense, I grew up to be an adorable person”

“I bet you did”

* * *

 

I never thought doing homework would be any kind of fun. But it was. All the odd numbers from page 83 were done within an hour while Sam and I talked nonsense for the entirety of those sixty minutes. My Chemistry homework and Sam’s Biology assignment were finished in the hour after that. Just by the end of the acids list on my notebook, a sweet and spicy smell got to Sam’s room and my mouth started watering with ideas of what we were having for dinner. And then I remembered, I never told my parents I was coming here.

“Oh, crap!” I took my feet from Sam’s bed and got up from the chair I was sitting on. My backpack had somehow landed on the opposite corner of where I was so I threw myself to the floor and looked for my phone. I always leave it on mute because my mom likes to check up on me and having it ringing or vibrating during classes is very distracting and- yeah, I don’t chat with many people. I'm never able to remember turning the volume up again and this time was no different.

**_(27) Missed Calls:_ **

**_(23) Mom_ **

**_(4) Dad_ **

“What happened?” Sam asked, obviously worried and kinda freaked out by my sudden panic attack.

“I forgot to tell my parents I was coming”

One ring. Two rings. Three rings. She can call me twenty three times but when I call back she can’t pick up her phone?

 _“Jessica?”_ My mom’s voice on the other side of the line sounded somewhat angry but also worried and I felt guilty for a second.

“Um, hi mom”

_“Don’t ‘hi mom’ me, young lady. May I know where on Earth are you right now?!”_

“At a friend’s house. I was- Err… Doing homework?”

_“Come on, Jess. At least think of a good lie, would you?”_

Yeah, I don't blame her for not believing me. I'm more of a  _Do-homework-on-Sunday-at-11pm_ person.

“It’s not a lie, mom. I actually just finished all the homework I had”

_“Fine. And who is this friend, again?”_

“S… Sam Winchester…?”

There was silence on the other side of the line and I wasn't sure if my mom was deciding if whether _‘Sam Winchester’_ was a girl I just befriended or a potential boyfriend. After my sister coming out to her, my mom has been torn between letting me hang around boys instead of girls or vice versa. If she only knew that the reason why I'm 100% sure I don't like girls is because I've already tried.

 _“Ok”_ she finally said _“I guess I have to thank your friend for making you work on Friday. You're also having dinner there I suppose”_

“Mmhmm” I was so relieved that she didn't question me about Sam. I didn't want to explain the whole _‘he won't try anything because he’s gay’_  thing to her, especially because he was right next to me.

_“Call when you're on your way home, ok?”_

“Ok, mom”

_“I love you, Jessie”_

I rolled my eyes. I hated it when she called me like that.

“I love you too, mom” and the call ended.

“She’s a little overprotective sometimes” I turned to tell Sam. And I immediately regretted my words. _Stupid, stupid, stupid, stupid, stupid, stupid, stupid._

“Yeah, Ellen does that with Jo too”

_Stupid, stupid, stupid, stupid, stupid!!!!!!!!_

“Crap. Sam- I’m sorry I-"

“Don't worry about it” he half smiled, but I still felt like human garbage.

 _“Ellen, we're home”_  we heard a male voice downstairs. It sounded too young to be Sam’s uncle so I assumed it was Dean  _"We brought pie!"_

“Let’s go” Sam told me and he left the room, I followed.

 _“I honestly don't know why you haven't moved in with us already”_  a man’s voice said and some laughs followed that sentence.

“Because I need a place to receive Dorothy in the holidays. Besides, your house is awesome Mr. Singer, but I don't think it could contain my coolness”. As we went downstairs I could see a redhead girl standing next to Dean and Uncle Bobby (I don't know when I started calling Sam’s uncle “Uncle Bobby” in my head). I recognized her, she went to school with us and had recently graduated. Her name was Charlie.

“You did _not_ just say that” Dean told her, sounding annoyed. But he was smiling at her. He looked up and his eyes landed on me, he seemed surprised and kind of amused “Well, what do we got here, little brother?” he said once we were at the end of the staircase.

“Uncle Bobby, Dean, this is Jess. Jess, these are Dean and my Uncle Bobby. Oh, and you probably remember Charlie” _Probably?_ It’s a little too hard to forget the person who broke into the school radio almost every morning to announce the highlights of the last episode of Game of Thrones, Breaking Bad and Doctor Who each week, and who hacked the scoreboard system of the gym to write _‘Stay gold, Pony Kids’_ before she graduated. The answer was yes, I did remember Charlie.

“Yeah, I remember her” was my answer “It’s a pleasure to meet you all”

“Wait, you're a friend of Sam’s from school?” Dean said “I don’t believe I hadn't seen you before” he smirked and raised an eyebrow at me. I couldn't tell if he was like that all the time or if he was actually flirting.

“Too bad” Sam answered before I could come up with a response "Let's go, I'm starving"

"Same here" Charlie added.

Sam and I helped Ellen fix the table and bring all the dishes from the kitchen to the dining room. It was a six person table, good thing Jo wasn't there that night. Uncle Bobby sat at one end of the table, Dean sat at his left and next to him was Charlie; Sam and I were sitting in front of them and Ellen was sitting opposite Uncle Bobby

* * *

 

Ellen was a thousand times better cook than my mom, I have to say it. And my mom's cooking skills are one of her finest features (if not the only one). Dinner was full of jokes about Charlie taking food from them and Dean being too busy with his car (which he repeatedly called  _'Baby'_ ) to be involved in any kind of actual human interaction. Until the conversation was turned to us. _  
_

"So, how was your homework, guys?" Ellen asked Sam and me.

"Homework" Dean snorted "Is that how kids these days are calling it?"

Sam's  _'Shut up or I will shove that fork up your ass'_ face was priceless. Dean's comment was really out of place, though.

"So far I don't believe there's a new name for the assignments teachers send students to do at their houses so yeah, kids these days still call it homework" I answered.

"Girl's got sass, I like her!" Charlie pointed out.

"Hey, get your hormones down" Dean told her.

"Geez, chill out gay police. I wasn't flirting!" And everyone started laughing, apparently Charlie and Dean were the entertainers of the house.

"Well, I'd be flattered" I said "Back to the homework thing, I don't know how Sam did it, but we finished it all. My mom wouldn't believe me when I told her"

"Yeah, I really don't know where he got the nerd" Dean said.

"Don't listen to him, Sam" Charlie said  "You're _pawsome_ " and she extended her fist over the table, Sam extended his and bumped it.

" _Really?_ "Dean asked, clamping the bridge of his nose " _Pawsome_?" _  
_

"Yeah, it's like, awesome but with a little bit of cute in it, _Pawsome"_ Charlie explained

"I know what it is- I mean, I guess but- Ugh, nevermind"

* * *

 

Food had almost disappeared from the table when we heard the doorbell ring.

"Seriously? She left her keys again?" Dean said

"No, Jo told me she was staying at Becky's. Are you expecting someone?" Ellen asked in a general way. Everyone, including Charlie shook their heads. i didn't feel like I had to, it was obvious I wasn't expecting anyone since it wasn't my house.

Dean stood up and walked to the window at the left side of the door, his easy expression turning into a scowl after he peeked through it. He turned around and rolled his eyes.

"Someone's looking for you, Sammy" he returned to his chair and poured more water on his glass.

"Please don't tell me it's-"

"Mmhmm" Dean answered before Sam finished the question.

Everyone in the room looked awkwardly at Sam, apparently I was the only one who didn't know who it was.

"If that kid keeps showing up at my door without an invite I'll have to chase him down with a rifle. Let's see if he gets the message then" Uncle Bobby spoke and there were no commentaries on that except for Sam's.

"Uncle Bobby, please" he said "I can handle this" Sam stood up and halfway between the diningroom and the door he stopped and turned. He mumbled a hissed "crap" and then looked at me.

"Jess I'm really sorry about this. You don't mind having Dean driving you home, right?"

"I haven't offered a ride" Dean said immediately. Charlie nudged his side just as fast "Ouch! I didn't say I wasn't going to"

"It's ok, I don't mind" I answered. But I _did_ mind.

"Great. Now, um- Ellen, can I-?"

"Go on, boy" Ellen replied. She sounded tired- no, resigned.

Sam left and no one said a word for several moments. It was the mother of awkward silences.

"Fiiiine" Charlie spoke "Dean, could you pass me the-"

"I swear to God I'm getting tired of that little freak annoying my brother, I wish I could-"

"Dean" Ellen kept him from talking "It's Sam's business and he has made it clear he doesn't want us interfering with it. Besides" she glanced at me for a second "we have guests"

"Right" he put some beans on his fork and said "Sorry Jess" before taking them to his mouth.

"It's ok" I said, thanking the fact that they still acknowledged my presence "But- Who did Sam just go to see? If you don't mind me asking"

"Well, you go to school with him, you should know" Dean said instead of giving me a straight answer.

"Huh?"

"Sam's douchy ex boyfriend"

"Oh, Gabriel?" I responded, wondering if Sam would be ok with us talking about this.

"Yeah, that one. I mean, I never really liked him but Sam was happy so whatever but now I can say what I want because they're not together anymore and if he was annoying before, now he's just a total pain in the ass-"

"Come on, Dean. Help me pick up the table" Ellen stood up, clearly upset with Dean's rant. Passive-aggressive Ellen is scary. Note to self: Do not mess with her. Not even by accident.

Dean got up with a groan and an "excuse me" before following Ellen with both his and Charlie's plate in his hands, leaving me with Uncle Bobby and Charlie- no, make that just Uncle Bobby.

"I'll go help them" Charlie said. 

So, I was sitting there. With Uncle Bobby. Whom I'd just met. Right after discussing his nephew's former homosexual relationship. Not. Awkward. At. All.

And it was obvious that the whole  _'help me pick up'_ was to make Dean shut up because Uncle Bobby was still eating. _  
_

"I guess apologizing for that idjit won't make any difference" he was the one to speak first.

"Excuse me?"

"Dean always gets carried away when he talks about Sam and his ex boyfriend" he seemed calm, picking pieces of meat and carrots with his fork, bringing them to his mouth and chewing slowly. 

"But Sam doesn't like to talk about this, right?"

"He asked us not to" he replied. And he kept quiet when Dean showed up to pick up the remaining dishes. "He said it was something he wanted to take care of himself" he continued after Dean was gone "It's his air headed brother the one who's having the most trouble respecting his wishes"

I didn't say a word. To be honest I felt the most uncomfortable I could ever feel. This morning I knew about Sam just as much as everybody else in school and the longest conversation I'd had with him was to tell him that the History teacher wasn't coming to class. And now I was at his house, discussing his love life with his uncle at his dinner table. Man, life is weird.

"I've known Sam for years" I began "But I don't know him that well. Still, he seems like the kind of person who can find a solution to everything" and I chuckled "He even got me into doing homework today"

Uncle Bobby smiled.

"Ellen and I want to believe we've done our best taking care of those boys. But sometimes it seems like, to Dean, it's still just the two of them against the world. If it wasn't for Sam, Heaven knows where would Dean be"

I didn't have an immediate response but the smile showed up by itself. I was glad to see Sam was the same at home and at school. He was definitely the kind of person I wanted to be around.

"I believe you've done a great job" I said.

 _"All I'm saying is, I could easily make that asshole stop showing up here"_ Dean was talking to Ellen as the two of them, plus Charlie, got out of the kitchen. 

"So can Bobby, but you don't see him actually chasing the kid down with a rifle, do you?" Ellen answered.

"And it's not like I don't want to" Uncle Bobby said once he heard them. 

"Boy, that would be a show" Charlie spoke

"Hell, it'd be awesome" Dean answered. I could tell by his face he was actually imagining it. What could Gabriel had possibly done to have Sam's family hate him so much?

"You two, stop that" Ellen popped Dean's dream bubble "it's  getting late. Jess, you should go pick your stuffs for Dean to take you home"

I went upstairs and stood at the door frame a little bit longer than what I had planned, recalling the entire evening. I had a really good time. And I was doing homework! Sorry, I'm still a little shocked by that. I walked to Sam's desk, where all the books were still out of place because of me. I arranged them and took a last look at his copy of The Little Prince.

"I cried when the Fox and the Little Prince parted ways" I said out loud, knowing there was no one there to hear me. I never tell that to anyone, I don't know why. It would've been nice telling that to Sam.

Sam's room was facing the front yard. I'm not sure with what purpose I looked out. _Right, you don't know. My subconscious_ wanted to see if  Sam and his ex were still there, it had been a while. They were still talking for what I could see, Sam was holding a box, it was rather large but small enough to be carried.

 _"Jess?"_ I heard Dean's voice calling me out. I took my bag and ran downstairs, recalling I had to text my mom or call her or whatever. I just decided not to.

"All set" I said when I saw him standing at the end of the staircase.

"Charlie, get off that couch. You're not staying the night"

"Boring" she replied "But I can walk home"

"You crazy? I'm not letting you walk home by yourself"

"One: Yes, I am. And two: Are you implying that I can't take care of myself?"

"I'm implying that I'm not a crappy friend so stop whining and come over"

Charlie got up groaning and complaining, took her bag from the chair at her right and joined us at the entrance.

"It's been a pleasure, Mr and Mrs Singer" I told them before leaving.

"Bobby and Ellen is fine" Ellen told me. Works for me.

When Dean opened the door, Sam and Gabriel, who were standing at about three feet from each other, stopped talking and looked at us.

"Mind saying goodbye to your..." Dean said to Sam.

"Homework... buddy?" Charlie finished.

Aaand the two of them walked/ran to Dean's car, parked by the sidewalk. This family has a thing with leaving me alone facing uncomfortable situations.

"Could you excuse me for a second?" Sam said to Gabriel. Have you heard the saying  _'If looks could kill'_?... If it were up to Gabriel I would've been cremated already. Sam walked to me before he gave him an answer.

"Well, this is awkward" I said in a quiet voice. We were far enough but I still felt like Gabriel could hear me, or at least was trying to. He was intimidating for sure.

"I had fun today" Sam ignored my commentary "Maybe we could do it again?"

"Sure" I replied, smiling "Hey, I like your family". Is it weird that I congratulated myself every time I made him smile? Ok, nevermind. "I can tell why you're so sweet" Did I really say that? UGH. No, wait, he's smiling even more. Yes.

"I can't wait to meet your family then" Crap. What have I done.

"Every rule has its exceptions" I said without thinking. "See you on Monday" I rushed to the car before my mouth spilled anything else.

I climbed to the back seat with my face looking red as Rudolph's nose, repeating to myself I had nothing to be embarrassed about. No, I did. I had subconsciously flirted with a potential new friend, in front of his ex boyfriend. And he wanted to see me again? Maybe he said that to be polite.

"Where to, ma'am?" Dean's voice brought me back to reality.

"Oh, Keaton and Ollers. Right in the corner" I replied.

"Ok, then. Charlie's house is closer so we're leaving her first"

"No problem"

The road to Charlie's house was full of classic rock and inside jokes between Dean and Charlie. They seemed to know each other so well, I longed a friendship like that. When we got to Charlie's I couldn't believe she wanted to walk all the way there from the house, it was a five-story building in a dark, seemingly dangerous neighborhood. 

"Nice meeting you, Jess" she said, I smiled in response "Lunch tomorrow?" she addressed to Dean and he nodded "Peace out, bitches", and she was gone.

"I'm no taxi driver, Jess. So move over" I got off the car and took the passenger seat.

"Keaton and Ollers, right?"

"Yup"

"So tell me, what's a pretty girl like you doing with my lame brother?"

"Is this flirting or interrogating? I really can't tell" Up to this day, I believe it was neither. I think it was a test.

"The thing is, Jess. Sammy might be a sugar coated six foot tall puppy, but he doesn't have that many friends. I mean, there was this Garth dude who's even lamer than Sam but he moved away and got transferred so that was it, and there's also Charlie but they don't talk much since she graduated"

"And she's closer to you than to Sam" I added.

"Mmhmm. I think he's nice to people in a general way. Never lets anybody in"

"What about Gabriel?"

"I still don't know how that happened" he replied after taking a deep breath, probably holding back the curses "For what I could see it was just emotional manipulation all the way. But only the two of them know what that relationship was really about"

We didn't say a word for the next few blocks.

"Sam seems to like you a lot" he said when we were arriving to my house.

"I like him too" I answered "he's really nice"

"Just- Keep this in mind" he continued speaking. We were already at my house, he didn't even ask me if that was the one, he just pulled over at the corner between Keaton and Ollers "What Sam needs right now is a friend. So if you're planning on becoming something else, you might wanna hold your horses for a while" That weirded me out a bit. Was Sam's brother actually telling me not to flirt with him?

"I'm not planning anything" I replied, slightly offended "And it's not like Sam's gonna change his mind overnight"

"Change his mind about what?"

"About- about being into guys" Yeah, I still felt uncomfortable saying it out loud in front of his relatives.

Dean stared at me as if I had just told him the sun was green.

"Sam's not gay" Dean stated, matter-of-factly

"But-" Ok, what's going on.

"Gabriel's been his only partner but he got us all sitting in the living room one night to tell us he's not _only_ into guys. I thought you knew"

Well, I didn't.

"Sam's pansexual"

Now, that was a game changer.

**Author's Note:**

> You have no idea how long I've been planning to write this. And when I started, it took me ages. I'll start writing Sam's POV later. And since this is a double story you'll get Deans and Cas' points of view as well. I'm thinking about writing Charlie's and Gabriel's too as a bonus (so no complete chapters like the other four). Just to fill in some blanks and for comic relief.  
> It wasn't really my intention but I believe Gabe will come out as a villain here (I'll do my best to make him a lovable villain, I promise)  
> Sorry if this Jess doesn't fit the one in your headcanons but this is what I came up with after rewatching her appearances in the show.  
> I hope you liked this, stay tuned for the other parts of the "Somebody Told Me" series (Yes, it is totally based off the song by The Killers)


End file.
